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Synfacts 2008(8): 0871-0871
DOI: 10.1055/s-2008-1078541
DOI: 10.1055/s-2008-1078541
Organo- and Biocatalysis
© Georg Thieme Verlag
Stuttgart ˙ New York
Dynamic Kinetic Resolution of α-Amino Acid Esters
D. A. Schichl, S. Enthaler, W. Holla, T. Riermeier, U. Kragl, M. Beller*
Leibniz-Institut für Katalyse e.V. an der Universität Rostock, Sanofi-Aventis Frankfurt and Evonik-Röhm GmbH, Darmstadt, Germany
Further Information
Publication History
Publication Date:
24 July 2008 (online)
Significance
A useful transformation from racemic α-amino esters to enantiomerically pure amino acids is described. The amino esters are racemized in the presence of catalytic amounts of salicylaldehyde 1 via the deprotonation of an imine intermediate. The combination of this racemization with an ester hydrolysis catalyzed by alcalase®, an endoproteinase of the serine type, leads to the corresponding acids in high yields and high enantioselectivities. Five different amino acids were synthesized in high optical purities with the developed method.